ACT I

Groggily awoken after a short and fitful night of sleep, I briefly wonder what in the world I'm doing here.

Then I remember that chasing First Class flights often means connecting through various US airports on my way to and from Toronto, and that my travails this week on Cathay Pacific First Class – as they did last year on Lufthansa – have brought me here to Boston on an overnight layover.

I quickly freshen up and pack my bags, hoping to catch the next airport shuttle to Logan Airport's Terminal B in time to beat the early morning check-in rush for my 6am commuter flight to Toronto. I'm flying economy class on this short segment – a cheap no-frills ticket booked using Aeroplan Market Fares – and so every precaution must be taken.

I punch in my flight number to Google Search to do a routine check of the flight status. AC7677.

Lo and behold, in big bold text on a red background: CANCELLED.

Confused, I check my itinerary on the Air Canada website. Indeed, it looks like the early morning flight has been shuttered, and I've been automatically rebooked on AC7619, which departs four hours later at 10:25am, and gets me into Toronto after midday. This is a problem, since the whole idea was to get back in time for work on Monday morning.

I quickly ring up Air Canada, only to hear the customary message of "...due to unusually high call volume, the current wait time is between 29 and 39 minutes...", which comes as no surprise. As the minutes tick by, I log onto ExpertFlyer and start checking for alternative flights.

There's a series of United flights via Newark that'll allow me to make it to work, but the problem is that the Boston–Newark flight is departing at 5:10am, 30 minutes from now. So that's off the list.

There's Porter flights that might work, but I don't think Air Canada is able to reissue my ticket on those airlines. My suspicion is confirmed when the Air Canada ticketing agent takes my call and tells me that there's no ticketing agreement in place with Porter. I also ask her why the 6am flight got cancelled; she says she doesn't know.

The last option is to catch the 6:30am flight from Boston (BOS) to Montreal (YUL), connecting on to the 9:30 flight to Toronto City (YTZ). I'd get into Billy Bishop Airport at 10:40am, which is awfully late for work, but nothing an apologetic text message to the boss won't fix.

I give the agent the green light to reissue the ticket, head downstairs to catch the airport shuttle, and rest easy thinking that the day was back on track.

ACT II

Interior, Air Canada Flight 8455 economy class cabin, day.

Our plane is taxiing towards the runway, ready to take off on the short 50-minute hop across the border to Montreal. The sun has risen, and my spirits are in the process of following suit.

Suddenly, the captain comes on the PA to tell us that we're experiencing a "maintenance issue" and that we're going to "hold our position just short of the runway and investigate", adding that it should be resolved "in five to ten minutes".

With one eye on my connection time in Montreal, I remark to myself how that doesn't sound promising at all. Happily though, five minutes later, we do indeed start moving towards the runway again.

I watch the Delta and United aircraft ahead of us take off successfully, before we line up with the runway and fire up the engines...

...only for them to sputter, our takeoff roll grinding to an agonizing halt.

Captain Obvious comes back to tell us that "the maintenance issue has not resolved itself", which leaves us all rather displeased to say the least. We're going to have to taxi back to the gate and deplane, since it's apparently very likely that the aircraft itself will have to be swapped out when the flight does eventually depart.

Back in the gate area, we're all lining up for the Air Canada service desk. Word quickly filters through that AC8455 is getting delayed to 10:50am (!), and since there's another Montreal flight at 10:40am (AC8457), everyone's getting rebooked onto that one.

I look on ExpertFlyer again for alternatives, but since the two early morning flights out of Boston have both gone pear-shaped, all the other flights – including AC7619, the 10:25am Toronto flight I was originally rebooked on – are now full. I regret everything.

Oh, and still no one knows why the 6am Toronto flight got cancelled in the first place.

I collect my new boarding passes, which now have me going BOS–YUL–YTZ and getting me into Toronto at the sad hour of 2:40pm. A hasty phone call to my boss explains that I'm trapped in Boston and won't be making it into work today. She laughs and tells me there's nothing to worry about.

ACT III

Interior, United Club Boston, day.

Here's a crash course on the layout of Boston Logan Airport Terminal B that you never knew you wanted. As you can see, pretty much the whole terminal is connected airside, with the exception of Gates B1–B3, which are used exclusively by Air Canada.

This means that accessing the airport lounge as an Air Canada passenger involves clearing security at a different part of the terminal, before re-clearing security at Gates B1–B3 before your flight. With another three hours to go before any hope of getting out of Boston, I had decided it was worthwhile to do exactly this.

I arrive at the United Club Boston and present my documents. "I'm flying Air Canada, but it's a complete sh*tshow over there," I explain to the front desk staff.

"What did you just say?!" she replies, as she scans my boarding pass. I look her in the eye, take my boarding pass, and walk into the lounge.

As I snack on a smorgasbord of stale breakfast pastries, I research my options in terms of demanding compensation from Air Canada.

Unlike weather-related delays, a mechanical issue is certainly something that's within the airline's control, and so the fact that I had to miss work because of these delays is something Air Canada ought to be on the hook for. And that's not even considering the mysteriously cancelled 6am flight.

I pass the time typing up the Impressions from China 2018 post. Since the Air Canada flights are departing from all-the-way-over-there, there's of course no indication of any Air Canada flights on the lounge's departure screens, let alone boarding announcements.

Since boarding for AC8457 was supposed to be at 10:10am, I head back to Gates B1–B3 a few minutes past the hour.

ACT IV

Interior, Gates B1–B3, day.

"Back again?" says the same TSA agent who scanned my documents all those hours earlier. "I hear there's been another delay..."

Indeed, I'm back at the Air Canada gates, and things are bad.

AC8455, the 6:30am Montreal flight that couldn't, is now cancelled as well. Instead, its rescheduled 10:50am departure has now transformed into a ferry flight without passengers; in other words, the aircraft is being flown all on its own back to Montreal for repairs.

Meanwhile, AC8457, the original 10:40 departure to Montreal on which most of AC8455's affected passengers (including myself) had been rebooked, was now delayed until 11:40, because the replacement aircraft hadn't arrived from Montreal yet. This was particularly bad news for me because it would jeopardize my connection to Toronto, possibly delaying my return home until 3:40pm!

At this point, I was exhausted. My body was still on Asia time, I had been up since 3 in the morning, and I had just gotten off a 15-hour flight the previous night. And as extraordinary as Cathay First was, no amount of First Class comforts can make up for a morning like this, when it seemed like everything that could've gone wrong, did.

Thankfully, Air Canada Concierge staff member Stephanie had arrived on scene to hear my frustration. I explained to her that I had originally been booked on AC7677, the 6am flight to Toronto, and was now caught up in a series of never-ending delays on the Montreal flights.

She immediately went about making things right. AC7619 to Toronto – the flight I originally got rebooked on, but then switched away from, thinking I was soclever – had suffered a delay as well, now departing at 11:20am. As I had seen on ExpertFlyer earlier, economy class was full on this flight, but there was still space in business class! Stephanie worked her Concierge magic and plonked me in Seat 1A, sending me on the quickest route back home.

She also informed me that AC7677, the original 6am flight, had been cancelled because Air Canada wasn't able to get a crew out here to Boston in time – another factor that's entirely within the airline's control.

Lastly, Stephanie gave me a US$15 meal voucher so I could grab some lunch, and also encouraged me to reach out to Customer Relations to get compensated for having to miss a day of work. The only food establishment in that little corner of Terminal B was a Starbucks, so I treated myself to a chicken and bacon panini and a Venti Strawberry Acai Refresher.

I posted my story in the Canadian Air Passenger Rights Facebook group to solicit some feedback and make sure that I was well within my rights to ask for compensation for lost wages.

Finally, at 11am, I flicked through my little stack of boarding passes – AC8455, nope, AC8457, nope, AC7619, there it is! – before boarding the plane, holding my breath as we made our journey across Logan Airport's taxiways, and only releasing it once we were finally airborne. Five hours and twenty minutes later, I was finally on my way home.

The Boston skyline has never looked so good...

Lessons Learned

Flight delays and cancellations – known in the industry as "irregular operations" or IRROPS – are an unavoidable part of life for travellers. I'm always grateful and a little surprised that I don't run into these situations more often; indeed, this is the first time in a long, long time that I've been significantly affected.

Nonetheless, I wanted to use this anecdote to remind everyone of the best practices when you're hit by a delay or cancellation. For one, being able to research your best alternatives is key.

Using ExpertFlyer, you can see which later flights are available on your route, as well as any potential routing options through other cities. You can check the loads of these flights, which is of vital importance, since a full flight isn't going to be very helpful.

IRROPS are exactly that – irregular – and so the usual ticketing rules don't apply. You don't need to accept the alternatives that airlines give you; providing there are seats available, you can request that the airline accommodate you on your preferred routing, without incurring a change fee or a fare difference.

Meanwhile, keep in mind that senior airline staff can do things like upgrade you to business class when economy is full, so if that's the situation, it never hurts to ask. Throw your weight around if you have elite status, and if not, put on your most convincing look of hopelessness and exhaustion and go win that sympathy.

Lastly, I'd highly recommend my fellow Canadian travellers to join the Air Passenger Rights Facebook group, where founder Gabor Lukacs has a long and storied history of helping Canadians "win" against the airlines. I'll be filing my complaint and compensation request with Air Canada Customer Relations using Gabor's excellent template.

Conclusion

This was one of the strangest days I've had in recent memory, when it seemed like the forces of the universe were conspiring to keep me stuck in Boston forever. Thankfully I lived to tell the story, one which I hope acts as a reminder to my fellow travellers that IRROPS can sneak up on you when you least expect it, and that it's best to remain aware of the best practices for if and when they do.

About Ricky
Ricky’s love for travelling and learning more about the world is unbounded. He’s on a mission to document and understand every square inch of the globe, and travelling on points will be an essential tool along his journey.